Divorced and Feminine

 

Quick Money

 

Harland was a sissy poster. He wanted one thing, and that was views and attention. He found out that the greatest accounts were either original creators or distributors of great content. People had become too lazy to fact-check whether his postings were legit or created for others. They were simple people, they saw a sissy caption, they liked and sometimes commented something promiscuous under his media. Within weeks, he’d amassed a thousand followers and a thousand more in page views. He was living the dream, setting up his account to begin generating revenue with every page view and post interaction, all while not risking his safety or privacy.

Harland wanted passive income, and seeing the opportunity of smut accounts getting thousands of views, jumped on the wagon. He wasn’t a girl, nor had a reliable source of girl pictures to post, so the next best was sissy captions. He’d spend considerable time browsing various subreddits and Twitter pages, collecting data on what did the best, and forced feminization vastly outperformed other sub-genres. The idea of female domination and being forced to dress as a girl was a popular fantasy for many, it seemed, and Harland took months of preparation, collecting various media to post.

It was simple: he’d post on Fridays once a week with a few captions, let the followers consume his posts for the week, and repeat the next Friday. It was easy, and by following various creators, collecting took no time at all. This side hustle became a big secret for Harland, but smut always sells. It was embarrassing to anyone to his genius money-making operation, because they wouldn’t understand he was solely in it for the money.

Until he wasn’t. The thing about media consumption is that no matter how much you convince yourself it’s for another reason, sooner or later, your brain craves it. Harland convinced himself it was for the money, but a simple 15-minute excursion turned into hour-long sessions, or watching various videos and captions. Then it became, for the research, which took more time. If he found better content, then he’d get more views, he rationalized, spending a whole Saturday afternoon jumping from website to website, grabbing information. He was becoming consumed by the media, craving what was happening in these captions to become true for him. His desires reeked of desperation, as his mind toyed with the thought of forced feminization, how he’d feel, the thrill, excitement, humiliation of being forced to be a girl. His heart hadn’t beat that rapidly ever, but the fantasy that bloomed in his mind created a situation that Harland couldn’t escape.

Perhaps it was desperation, or the rapid heartbeat, or even the lack of blood in his head, but Harland secretly broke down. The way to fast money led him down the path of sissy captions and slowly turned him into a sissy. While his roommates were away for Valentine’s Day dinner, Harland snuck into their room. They all had girlfriends, one of whom was staying the night for Valentine’s Day fun. Finding her duffel bag on the bed, he smiled, carefully unzipping it and looking inside. He moved clothes around until he found a pair of white lace panties.

Feeling the fabric for the first time made Harland’s eyes dilate. He’d never touched a pair before, and he dropped his pants, sliding the pair up his legs. He loved how they felt tightening up his legs, and even more as they were adjusted into place. He looked down, loving the feeling, taking in the moment. Then he heard the door to the apartment unlock. Panic settled in as he hurriedly grabbed his pants and ran for the adjacent bathroom. He shut it quietly as his roommate's voice called out. Seeing the light on, he knocked, telling Harland he’d be gone for the night. Harland, wearing that roommate's girlfriend's white lace panties, grunted in acknowledgement, listening as they left. He breathed a sigh of relief, putting his pants on and returning to the safety of his own room. What he didn’t know was that his laptop was open to his sissy blog, and the girlfriend, who saw inside, was about to put two and two together when she returned, and her panties were missing.

Days passed since the Valentine’s Day incident, and Harland thought nothing of it. He’d slept in the panties, enjoying their feeling for the evening, and decided to wash them and return them to the roommate. Sliding them under the bed, Harland thought it would be a good excuse for their sudden disappearance.

One day, he received a DM from his roommates’ girlfriend. They’d been following each other on social media, occasionally liking posts, but had little interaction besides that. Her message was long, and the length worried Harland, who’d hadn’t read the content. It told Harland she knew he’d taken her panties, and she’d be giving them back to him. She saw his sissy blog on his screen and put two and two together. She’ll be over, without his roommate soon to discuss things further.

Harland began sweating at the thought of what might occur. All those months of reading various captions and posts flood into his mind, ballooning his mind and filling it with “what ifs.” Thoughts and ideas that were not likely to come to fruition, but the idea was beginning to excite him. What if he experienced one of those posts or captions, he’d read about?

Hours passed before a knock at the door brought Harland back down to earth. He was worried about her reaction, slowly opening the door. She barged in with a duffle bag, and before the door closed asked if anyone was home. Harland shook his head, his roommates wouldn’t be back for hours. This was typically his time alone.

“Strip.” She said bluntly. Harland was confused by the request until she gestured for him to quickly do it. In the living room, Harland dropped his pants and took off his shirt. The roommate’s girlfriend giggled at his appearance, making comments that he was on the right path, he’d be better off as a girl. This both angered and excited Harland. He was beginning to live out the fantasies of the captions he’d read about.

She tossed him a pair of panties, the same white lace ones he stole. “Don’t worry, you can keep those perverts.” Harland put them on as she watched and smiled, continuing to emasculate him. She proceeded to toss him a matching white bra and a thin white floral dress. Slowly, Harland put it on as she took out her phone and snapped a picture.

“What was that?’ Harland asked, his voice trembling with embarrassment.

“Collateral,” she smiled. “See, I’ve always wanted to have a sissy pet. And I want to make sure this stays between us. You tell anyone about this arrangement; these pictures get sent to everyone on campus, and you get exposed as the sissy you are. Don’t worry, they won’t be seen by anyone but me.” She smiled. “Now pull up your skirt and show off those panties of yours.”

Harland shook his head. Being feminized was enough, but posing for photos was where he drew the line.

“Let me reframe this,” she said coldly, stepping closer. “Pull up your skirt and show off those panties, or I'll send this picture to my boyfriend and explain that you took my panties. How is that going to look?” Harland was stuck, and he was slowly realizing it.  

Harland lifted the dress to cover his face, hoping his bulge wasn’t showing too much. It was embarrassing enough. She laughed, taking numerous pictures, front and back.

“So I did some research,” she continued, sitting Harland down and pulling out some instruments from her bag. “I know you like quick and easy money. I mean, that’s why you made your blog, right?”

Harland didn’t answer. She began working on putting on a dirty blonde wig. “Well, I know a place where sissies can make a few extra dollars, and I thought if you liked sharing that content, I’m sure you’ll be interested in going.” Harland didn’t say anything. He didn’t know what she was alluding to, and he was scared to ask for clarification.

For the next hour, she delicately did Harland’s makeup, did his nails, and fixed his wig. Finishing by putting him into some knee-high white boots to finish the look. She smiled, excitedly taking a picture before pulling him outside. Harland felt nervous walking down the hall. What if his peers recognized him? What if his roommates came back early? They stopped outside as the roommate's girlfriend took a step back.

“Pose, girl!” she smiled, and Harland struck the only pose he could; dolled up, worried, and confused.

They then drove over to the other side of campus, Harland trying to catch as many landmarks as possible and street names in case he had to walk back home. He didn’t have his phone or wallet, spelling trouble if he had to get back to the apartment after she was done tormenting him. They pulled up outside a brick building that Harland never knew existed. There were stores adjacent to this building, and they were generic businesses, a laundry, and a bookstore. She got out and opened his door.

“Come on,” she gestured, and uneasily, Harland left the car. She knocked on the business whose windows and door were taped up. After a few moments, it opened, and they were ushered inside. The interior did not match the uninviting exterior.

The inside was darkly lit, but the lights they did have were bright pink and blue. They were in the process of setting up for an event, bartenders cleaning the bar, servers setting tables, and dancers on the stage. Not any dancers, erotic dancers, wearing various outfits, talking to each other while others worked around them. The man who granted them access hugged the roommate’s girlfriend and began whispering to her. She nodded, and he took out some cash before handing it to her.

“You always know how to find them,” he laughed. She tucked the money away.

“Please don’t break him,” she laughed, pulling Harland closer to the man. “He’s fragile and hasn’t had this experience yet.” The man smiled widely, looking Harland up and down.

“Well, he has the looks of a good addition,” he said. “I’m sure the girls will love meeting him.” The man started guiding Harland towards the stage.

“I’ll be back after the lunch rush to pick you up!” she called back walking towards the door. “Just remember not to lose all your masculinity.”

Unwanted Territory

 

Swap Class - Crosby

 

StitchFix Order

 

Aunt’s Birthday Present

 

Supportive Friend's - Extended Cap

 

Dawes recently got dumped by his girlfriend. He thought everything had been going well until one night he got a call that ended with “we need to go our separate ways.” While initially upset and hurt by the decision, a new sense of clarity and strength emerged from the loss. An opportunity to be a better, more fulfilled version of himself became apparent. He realized that for years, he never allowed full exploration or self-expression to be apparent, instead allowing himself to conform to those around him. Today was the day it stopped.

Dawes was a straight man; he loved women, and the only sex he’d had any interest in was women. Despite his masculinity, Dawes had a secret side to him, which only a few people knew; he liked cross-dressing. In his teens, he’d enjoy frequent cross-dressing sessions, wearing his sister’s clothes when home alone, but as he grew up, the thrill of wearing women's clothes morphed into wearing panties and wearing women’s shorts. Rhett knew that much, and for the last few years, he’d been wearing exclusively women’s panties. Some were flashy, with various styles, designs, and fabrics, and others were more basic with solid colors. Either way, he’d stopped wearing boxers years ago and only wore panties. One of his ex-girlfriends knew that, and they didn’t particularly care, to his relief, as long as he didn’t try to wear their panties or wear thongs, which Dawes had no desire to do.

Dawes, now single, began questioning and exploring his feminine side. He was wearing shorter shorts in public, both as a boost for his confidence and to catch some sun. Dawes was focusing on being himself and not caring about others’ opinions. What he was wearing wasn’t wrong, nor inappropriate, so what did their opinions matter? He began reading and even writing various crossdressing and feminization captions as an outlet to explore this previously ignored femininity. As part of his progress, Dawes wanted to be more open about his feminine side and not lock it behind his mask of masculinity. He can be both masculine and feminine, keeping himself authentic and attracting people who are like him.

Colette was a close friend of Dawes. They’d known each other for years, and while there were no romantic feelings between them besides friendship, they often discussed intimate and personal details about themselves. There was no filter or judgment between the two as they joked. Following the breakup, Colette was the only person Dawes could seemingly be authentic to, so while planning a Christmas week adventure to the mall, Dawes took a deep breath and asked if they could visit Victoria’s Secret. Colette, without missing a beat, jumped at the idea and agreed.

When they arrived at the packed mall, they wandered through various stores as Dawes disclosed more of his feminine personality. Colette didn’t need the outright admittance, since she thought something was up when Dawes’s eyes lingered too long on the display lingerie at Victoria’s Secret. No judgment, as Dawes confessed his likings to women’s underwear, and his desire to be feminized.

Colette asked if they wanted to venture deeper into the store to see more lingerie, to which Dawes excitedly agreed. They wandered through various displays, discussing various styles and preferences. To Colett’s surprise, Dawes knew a fair bit about women’s lingerie, too much not be an enjoyer. Dawes confessed he liked lingerie; he’d bought a few sets for his exes who never wore them for various reasons. While he disliked that, Dawes expressed interest in owning a set himself that he could wear when he wanted to and not be reliant on another to dress for him. Dawes felt comfortable in his masculinity to wear a lingerie set, and why should women be the only ones to dress sexy?

Their day at the mall came to an end, as Colette and Dawes set up a date to exchange gifts before Dawes left to see family out of town. A few days later, Dawes, gift in hand, knocked at Colette’s apartment door. With a smile, she opened it, expressing surprise at Dawe’s wrapping and inviting him inside. Eagerly, Colette opened up her present and hugged Dawes for his gift. Dawes didn’t expect anything big in return, so when she handed him a box, Dawes eagerly opened it.

When the tape on the box split, Dawe’s life would change. Inside, he pulled out a plastic bag containing the red lingerie set he’d been gawking at a few days previously. Dawe’s stomach dropped, his breath shallow, his heart beating rapidly. This was the test to see if all those words he’d said about being comfortable with his masculinity were true, or if they were merely lies.

Dawes held up the lingerie set, taking it out of the plastic bag, his eyes getting wider as he looked at the beautiful set. He ran his fingers through the lace, the soft, textured fabric giving him goosebumps as he took it in. For years, he always gifted, never received lingerie, and now Colette had fulfilled a secret wish for him. Dawes felt conflicted, he really wanted to wear it to feel feminine and have a slight taste of the feminine experience. But he was nervous about the outward appearance of accepting and knowingly wearing lingerie. What would Colette think? What would future girlfriends think? Would they like it too, or would they judge him? Dawes took a deep breath, taking in the whirlwind of emotions. Why give their opinions weight?

“Go try it on,” Colette said, happily. She pointed to the bathroom.

Without hesitation, and perhaps too quickly, Dawes bolted to the bathroom with the box, locking the door behind him. He looked at himself in the mirror, heart still beating against his chest, like a part of him wanting to be free from the expectations and opinions of others. Dawes knew what he had to do. He threw off his shirt, unbuckled his belt, and dropped his pants, casting his masculine clothes aside. He was going to do it. And if he looked ridiculous at least, he could say he tried something he always wanted to.

First, he slid the red lacey panties up his legs. The lace seductively rubbed against the inside of his thighs, causing chills through his body and a bit of excitement. He pulled the pair up to above his waist, adjusting his junk, and tucking them between his thighs. Dawes admired himself in the mirror, running his hands on the lace, and enjoying the feeling against his body and hands.

Next, he unwrapped the bra and placed it against his chest. Dawes hadn’t worn a bra since his teenage cross-dressing years and didn’t remember how to put one on. He brought them back to the front of his chest, fumbling to connect the hooks as excitement coursed through his body. Finally, locking the clasps in place, Dawes pulled the bra around and put his arms through the straps, sliding into place. He liked the way it hugged his chest, and Dawes admired himself in the mirror, spinning around to see every angle his neck would allow him to turn and see. He felt undoubtedly feminine, sexy, and excited.

When he moved the box from the counter, he heard a rattling sound. Confused, he looked inside and saw a red collar. With Dawes' confidence sky high, his face turned a matching red to the lingerie as he looked at it. It matched the set, and why not? Adjusting the side, he put the collar around his neck, enjoying the restrictive and submissive feeling it provided as the leash fell down his chest.

Dawes smiled at the person he saw in the mirror, confident, sexy, embracing parts of him he never thought existed until recently. He was comfortable with himself and admitted he was a straight man who liked wearing lingerie. It was rare to have supportive friends like this, and Dawes was blessed and grateful for Colette. Taking a deep breath, he unlocked the door, stepping into the living room to hear her reaction, feeling more confident and sexier than he had ever felt before in his life.

 

A Friend’s Snap

 

Must Be A Phase, Right